Cl.C(N=C=NC[CH2:8][CH2:9][N:10]([CH3:12])C)C.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22]C=2N=N1.[CH:23]([N:26](C(C)C)CC)(C)C.[CH:32]1([CH2:40][O:41][C:42]2[CH:50]=[CH:49][C:45]([C:46]([OH:48])=O)=[CH:44][CH:43]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C1(CO)CCCCCCC1.CC[O:63][C:64](C)=[O:65]>CN(C=O)C>[CH:32]1([CH2:40][O:41][C:42]2[CH:43]=[CH:44][C:45]([C:46]([N:10]3[CH2:9][CH2:8][N:26]([C:64]([O:63][C:21]4[CH:22]=[N:14][CH:18]=[CH:19][CH:20]=4)=[O:65])[CH2:23][CH2:12]3)=[O:48])=[CH:49][CH:50]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]11-Ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (150 mg), 1-hydroxybenzotriazole (110 mg) and diisopropylethylamine (0.23 ml) were added to a DMF (5 ml) solution containing the resulting compound (190 mg) and 4-(cyclooctylmethoxy)benzoic acid (176 mg) prepared from cyclooctylmethanol with reference to Reference Example 70, followed by stirring overnight at room temperature. The reaction solution was diluted with EtOAc, the organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from EtOAc/hexane to obtain 3-pyridyl 4-[4-(cyclooctylmethoxy)benzoyl]-1-piperazinecarboxylate (240 mg).
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